Inside Sister Ship’s Dreamy Bar Mail Ritual

Image Courtesy of Faraway Nantucket

Tucked behind a weathered façade on Nantucket’s Centre Street lies a courtyard where time loosens its grip—ivy sways, jazz drifts, and the spirit of 1920s Paris flickers to life in the glow of golden hour. At Faraway’s Sister Ship, oysters arrive two by two on chilled porcelain, cocktails lean clever, and the mood lands somewhere between Fitzgerald fantasy and barefoot New England ease—think Gatsby in boat shoes, and someone’s just ordered a round of Paper Planes.

Image Courtesy of Faraway Nantucket

At the heart of the magic is a charming ritual called Bar Mail, a nod to the spirited correspondence between F. Scott Fitzgerald and Ernest Hemingway. “We were inspired by the idea that bars have always been places where writers, thinkers, and travelers cross paths,” says Jason Brown, co-founder of Blue Flag Capital. “Bar Mail lets our guests leave a piece of themselves behind—or connect with someone over a shared sense of curiosity.”

Image Courtesy of Faraway Nantucket

Here’s how it works: guests are invited to pen a handwritten note—sealed with wax, no less—and tuck it into the bar’s letter archive for future travelers to discover. Some messages are cheeky, others poetic. One came from a newly engaged couple who toasted their future and left a letter behind for “the next dreamer.” Another was just a sketch of a martini glass and the words: Get the scallops. Trust me.

Image Courtesy of Faraway Nantucket

“Writing with pen and ink creates this tactile, real moment that feels completely out of time,” says Brad Guidi, also of Blue Flag. “It’s storytelling in its truest sense.” There’s no app, no QR code—just a candle, a wax stamp, and a bartender who might pass you a note from someone who sat in your seat last summer. Ricki Millington, a director at Blue Flag, calls Bar Mail “a way to extend the spirit of Sister Ship beyond these four walls.” It’s part guestbook, part time capsule, and entirely irresistible to romantics, dreamers, and cocktail-fueled poets alike.

Image Courtesy of Faraway Nantucket

And while Bar Mail is certainly a draw, it’s far from the only reason to linger. Sister Ship’s menu balances New England coastal classics with bright Mediterranean flair, served in a candlelit dining room that feels like the after-party from a Wes Anderson film. Outside, the courtyard turns golden at dusk—an invitation to stay a little longer, write a little slower, and maybe, just maybe, leave behind a note for the next kindred spirit who stumbles in.